CHEBI:180696 - 20β-dihydroprednisolone

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name 20β-dihydroprednisolone
ChEBI ID CHEBI:180696
ChEBI ASCII Name 20beta-dihydroprednisolone
Definition A glucocorticoid that is prednisolone in which the oxo group at position 20 has been reduced to the corresponding β-hydroxy group. It is a metabolite of prednisolone.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter R. Stephan
Supplier Information eMolecules:36758523, ZINC000015568940
Download Molfile XML SDF
Formula C21H30O5
Net Charge 0
Average Mass 362.466
Monoisotopic Mass 362.20932
InChI InChI=1S/C21H30O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h5,7,9,14-18,22,24-26H,3-4,6,8,10-11H2,1-2H3/t14-,15-,16-,17-,18+,19-,20-,21-/m0/s1
InChIKey LCOVYWIXMAJCDS-FJWDNACWSA-N
SMILES [H][C@@]12CC[C@](O)([C@@H](O)CO)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)C=C[C@]12C
Metabolite of Species Details
Homo sapiens (NCBI:txid9606) Found in blood plasma (BTO:0000118). See: PubMed
Bos taurus (NCBI:txid9913) Found in urine (BTO:0001419). See: PubMed
Roles Classification
Biological Role(s): mammalian metabolite
Any animal metabolite produced during a metabolic reaction in mammals.
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
hormone
Originally referring to an endogenous compound that is formed in specialized organ or group of cells and carried to another organ or group of cells, in the same organism, upon which it has a specific regulatory function, the term is now commonly used to include non-endogenous, semi-synthetic and fully synthetic analogues of such compounds.
(via steroid hormone )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 20β-dihydroprednisolone (CHEBI:180696) has functional parent prednisolone (CHEBI:8378)
20β-dihydroprednisolone (CHEBI:180696) has role human metabolite (CHEBI:77746)
20β-dihydroprednisolone (CHEBI:180696) has role mammalian metabolite (CHEBI:75768)
20β-dihydroprednisolone (CHEBI:180696) is a 11β-hydroxy steroid (CHEBI:35346)
20β-dihydroprednisolone (CHEBI:180696) is a 17α-hydroxy steroid (CHEBI:35342)
20β-dihydroprednisolone (CHEBI:180696) is a 20-hydroxy steroid (CHEBI:36854)
20β-dihydroprednisolone (CHEBI:180696) is a 21-hydroxy steroid (CHEBI:35344)
20β-dihydroprednisolone (CHEBI:180696) is a 3-oxo-Δ14-steroid (CHEBI:77166)
20β-dihydroprednisolone (CHEBI:180696) is a C21-steroid (CHEBI:61313)
20β-dihydroprednisolone (CHEBI:180696) is a glucocorticoid (CHEBI:24261)
IUPAC Name
(20S)-11β,17,20,21-tetrahydroxypregna-1,4-dien-3-one
Synonyms Sources
(11β,20S)-11,17,20,21-tetrahydroxypregna-1,4-dien-3-one ChemIDplus
(20S)-hydroxyprednisolone ChEBI
20(S)-hydroxy prednisolone ChEBI
20β-dihydro-PRED SUBMITTER
20β-hydroxyprednisolone ChemIDplus
prednisolone EP impurity G ChEBI
prednisolone impurity G ChemIDplus
Manual Xref Database
27524368 ChemSpider
View more database links
Registry Number Type Source
2299-46-9 CAS Registry Number ChemIDplus
Citations
Deventer K, Polet M, Van Gansbeke W, Hooghe F, Van Hoecke H, Van Eenoo P (2021)
Investigation of the urinary excretion of prednisolone and metabolites after nasal administration: Relevance to doping control.
Drug testing and analysis 13, 1897-1905 [PubMed:34081842]
[show Abstract]
Van Meulebroek L, De Clercq N, Vanden Bussche J, Devreese M, Fichant E, Delahaut P, Croubels S, Vanhaecke L (2017)
Pharmacokinetic and urinary profiling reveals the prednisolone/cortisol ratio as a valid biomarker for prednisolone administration.
BMC veterinary research 13, 236 [PubMed:28806969]
[show Abstract]
Matabosch X, Pozo OJ, Pérez-Mañá C, Papaseit E, Segura J, Ventura R (2015)
Detection and characterization of prednisolone metabolites in human urine by LC-MS/MS.
Journal of mass spectrometry : JMS 50, 633-642 (Source: SUBMITTER) [PubMed:25800201]
[show Abstract]
Nebbia C, Capra P, Leporati M, Girolami F, Barbarino G, Gatto S, Vincenti M (2014)
Profile of the urinary excretion of prednisolone and its metabolites in finishing bulls and cows treated with a therapeutic schedule.
BMC veterinary research 10, 237 [PubMed:25267433]
[show Abstract]
Leporati M, Capra P, Cannizzo FT, Biolatti B, Nebbia C, Vincenti M (2013)
Determination of prednisolone metabolites in beef cattle.
Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment 30, 1044-1054 [PubMed:23510304]
[show Abstract]
Dodds HM, Taylor PJ, Johnson LP, Mortimer RH, Pond SM, Cannell GR (1997)
Cortisol metabolism and its inhibition by glycyrrhetinic acid in the isolated perfused human placental lobule.
The Journal of steroid biochemistry and molecular biology 62, 337-343 [PubMed:9408088]
[show Abstract]
Tembo AV, Ayres JW, Sakmar E, Hallmark MR, Wagner JG (1977)
Plasma prednisolone concentrations: comparison of radioimmunoassay and competitive protein binding assay.
Steroids 29, 679-693 [PubMed:898234]
[show Abstract]
Last Modified
27 January 2022